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Yes. To take an extreme case, imagine some rich guy who runs sweatshop gets very rich and retires and becomes activist against it.

Does that actually happen? Feels like it would normally be the opposite

Not sweatshops but Alfred Nobel might be one example.

I worked in corporate marketing for long enough to become an activist against surveillance capitalism.

Yes. Many cases of the "preach being the cover for the sin".

But that does not negate the truth of their new position on sweatshops